


CherryPoppin

by Attackofthehoes



Category: Star Wars, Star Wars - All Media Types, Star Wars Prequel Trilogy
Genre: F/M, Fluff and Smut, Loss of Virginity, Obi wan smut, Porn With Plot, Porn with Feelings, Smut, Vaginal Sex, Virgin Reader, Virginity Kink, realistic sex, star wars smut
Language: English
Status: Completed
Published: 2021-02-15
Updated: 2021-02-15
Packaged: 2021-03-17 07:48:16
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,909
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29468232
Author URL: https://archiveofourown.org/users/Attackofthehoes/pseuds/Attackofthehoes
Summary: An inexperienced Obi wan takes your virginity. Also mutual mushy feelings.• Please only read if you’re over 18, go elsewhere if you aren’t, I’m not comfortable with people underage reading this content, please respect these wishes.•
Relationships: Obi wan x Virgin, Obi wan x reader, Obi-Wan Kenobi/Reader
Comments: 1
Kudos: 35





	CherryPoppin

**Author's Note:**

> I’ll come back to edit this later. Sorry if it’s hard to read. Based on a tumblr anon for I saw about realistic sex and how it’s awkward at first. The anon was for KenobiKittens But I hijacked it. The facts are your not gonna cum the first time.

During your lunch break you would go to a cafe down the street. The bright upper level of Coursant shining mid day. That is where you first met your friend Obi-Wan, who frequented the coffee shop for tea. What started as sharing the only free table with a stranger, ended up blossoming into a friendship. When he was not away on a mission, you would hang out, help each-other study, and just enjoy the company. Over the months your banter had progressed. Now starting with joking innuendos, and ending with late night chats, about past experiences. He was very professional despite still a fresh 23 years. Putting the mission first, often leaving him with little spare time. He admitted though he traveled across the galaxy, he left only a handful of one night lovers behind. For several reasons you had just never gone very far, as were a bit self conscience of it. He had been gone for about 3 months now, he sent you a message on your comlink, that he had returned from a mission just two days ago, and would stop by later today after you got off work. You decided to put something nice on as a surprise. Standing in the mirror you started to wonder why you were doing this. You knew Jedi couldn’t date, not that you had time for that anyway. He had been a friend for a while but could you be friends with more? Perhaps with benefits? The tension and chemistry was definitely there.

You hear a knock on your door, nervousness and excitement hits you like a wave. Why were you nervous? You open the door “oh my god your hair!” You exclaim. It was now much longer, with no pony tail or braid. It was just above his shoulders. The beginnings of a beard growing. He shuts the door behind him. “I was made a Jedi knight” he says with a smile “after Qui Gon...” he continues dozing off. You realize how much older he looks now, reminding yourself that you’re both adults and have been for quite a few years now. Even if you didn’t feel ready to do adult things. “I’m so happy for you” you break the silence quickly. “Do you win anything?” you ask. “It doesn’t quite work that way” he retorts trying to hide a grin at your lack of knowledge. He bends down to unbuckle his boots and take them off. In your friends moment of weakness, you strike. Giggling you shuffle quietly and try to shove him over. Still taking his shoes off he avoids you, not even looking up. Your socks slide on the wood floor and you bump into the wall. Ego bruised. You try again this time not hiding your attention “Your not going to get me if you keep announcing your attack” he says referencing your pre attack giggles. You give a scowl. His back is too the wall, maybe he hasn’t noticed. This time you lunge right for him, fingers almost grabbing the heavy fabric of his tunic. Before you even realize what happened your backs against the wall, standing now where he was. “I didn’t even see you move!” You blink widely, a bit dizzy at the speed he had turned you around.

The golden sun set creeps through the windows. Illuminating your figures. Was he always standing this close? He leans in to kiss you, bending down to reach your lips. You on your toes to meet him. The kiss is messy, teeth clicking at first before finding a rhythm. Your fingers interlacing with his. Months and months of pining finally released. He pulls back, your eyes flutter open. “My apologies I shouldn’t have...” you wipe some shared spit from your mouth. “No I...I’ve been waiting for you to make a move” you smile unable to meet his gaze. “Maybe we should...discuss this” Obi Wan says and you awkwardly walk to the small living room sofa. During the rather uncomfortable conversation you inch a little closer to him. A moment later he closer to you. The energy in the air is palpable. “Your making me nervous” he admits with a half smile. “I’m making YOU nervous, you’re making ME nervous” you respond.

“I know I can feel you..I mean, it..your energy” he says quickly correcting himself. You feel your face red and throbbing. He takes the lead “maybe I could help you..relax then?” he murmurs, softly enough that if you weren’t paying attention, you would’ve missed it. He turns his body, facing you on the sofa crisscrossed as if meditating. You on your knees shoulders perpendicular. You lean forward eyes half closed, putting an arm on the cushion by his thigh to stabilize yourself. He sits forward meeting you. Eyes both shut it starts slow, it’s wet and occasionally bump into each other or accidentally bite his lip hard. At first you laughed it off but now you didn’t even waste the time. Hungrily connecting, only surfacing for air. You wanted to be closer, reading this he grabs you by the hips pulling you onto his lap. You dont even say anything just continued in your passion. Your hands on his shoulders, they felt to sturdy. You had waited so long for this. His lips were soft and supple. The kiss was gentle despite him being in control. You felt as if you were safe, taken care of. You were starting to sweat a little and felt very hot. You pull back and he opens his eyes as if not wanting it to end. “Will you, should I, can we” you start and he finishes your sentence with a reassuring smile. “Let’s move somewhere with a bit more room, shall we?” Neither of you say anything as you both walk with purpose to your bed room. Cringing internally at how your sheets were a mess and dirty clothes on the floor. He didn’t seem to even notice. You resume your kiss trying to negotiate onto the bed, with lips locked. Climbing back onto his lap, he holds your hips firm this time, moving down towards your ass and squeezing. Your arms around his neck, fingers pulling at his golden locks. You feel bold and pull his hair, guiding his head to the side as you leave hickeys. Sucking lovingly, emotions on high. His fingers find the edge of your shirt. “May I? He asks gently, sincerely looking to you for permission. “Please” you breathe out. He pulls your shirt over your head, you having to wiggle out of it a bit. You go to undo his ultity belt. He helps you with the buckle as you fumble with it, hands shaking. Taking off his double layers of tunic, leaving only the long sleeve undershirt that hugs his body. You sit back just taking in eachother, still mostly clothed, but the least you had seen of eachother. Seemly unable to look eachother in the eyes.

  
You could see his chest heaving, catching his breath. You gazed up his fit body, mind so full of thoughts that you entrusted your body to run on instinct. He gingerly ghosted his hands over your figure. Admiring the setting sunlight, projected on your skin from your half curtained windows. “We should’ve done this before” you pant out as he begins kissing your neck. “I wasn’t sure if you’d think I was being too forward” he responds, his hot breathe on your neck, teeth lightly brushing it. His lips a silky contrast to his scratchy stubble. “I didn’t want to scare you away. I’d rather have us as just friends than as nothing at all” he says honestly. This makes your heart swell. How was he so considerate. Were all Jedi this way? Moving with the kiss you had accidentally ground down on him. It felt good yet uncomfortable, as you wet underwear stuck to your skin under your pants. You could see him composing himself, so you did it again. Want to drive him mad. Grinding on him a bit harder, you could feel he was already half erect, no doubt struggling to keep focus. He stops sucking on your collar bone to take his last shirt off. His body is pale from lack of exposure under all the layers of fabric. It’s not overly muscular but fit and athletic. You allow you hands to wander from his shoulder to his V line. “May I rid you of this?” He asks running his thumbs under the back of your bra. “Mmm” you hum in response. He unclaps it and moves back a bit. Taking in the view of your breasts. His eyes scanning you, you become embarrassed and your arms come up to cover yourself. “You don’t need to be shy love” he whispers. “I’d like to see your beauty, if you’d let me” pulling gently at your arms, unfolding them.

You turn your face away unable to make contact. Your skin reacting to the cold with bumps and your nipples red and perky. He slowly slides his hands up your body hovering before your breasts. You nod still not looking directly at him. You could feel him fully hard through your pants and his. You bit your lip nervous but excited. He holds your boobs lightly before gradually giving a rougher squeezed. Gently rolling his thumbs over them and pinching them between his forefinger making you jolt. You catch a devilish grin out of the corner of your eye. You grow impatient. Foreplay is important but you needed these pants off. You get up off him, his warm hands leaving you and pull you pants off. Panties and all, just getting it over with. He swings his legs off the bed to face you, and gets up. You suddenly become aware of your actions and think your gonna faint. Your hands go to cover yourself again before he holds them in his own and kisses you where you stand. “I feel, embarrassed” you choke out. Tears prickling in the corners of your eyes from everything going on. Cringing at the wetness dripping down your legs, so obviously in need. Aching for a sensation you’ve never felt. The kiss is loving, reassuring. “You look like a goddess.” He says forehead pressed against yours. “We don’t have to keep going today.” He says to you, but you ignore this. The panties were already off. You get on your knees in front of him looking up. The obvious bulge straining again his pants. “Can I?” You ask and he nods biting his lip. You grab the waist line and pull his pants down as he steps out of them. Your hand hovers over his erection through his underwear. You flash an unsure look at him. He takes you wrist and guides you. His eyes shut tight trying not to make a sound as you palm him, slowly with more pressure. He grounds and you rub, making out the shape though feel. You pause. “Well aren’t you gonna take your socks off? Who fucks with socks” you say with bite in your voice but a smile on your face. He laughs and pulls them off then hooks a thumb in the elastic of his underwear and pulls them down. Still on your knees eye level as his cock is released from its confines.

He was fairly well groomed with freckles and moles like constellations on his body. It moves more than you realized, rising and falling with his breaths, twitching every now and then. His cock was red and veiny, it made your thoughts go wild. balls really do look like that huh? Is it rude to stare? oh god will that fit? He was about average size maybe a little bigger, thicker, but you were suddenly intimidated. He would’ve noticed this change in aura if he himself wasnt turned away blushing, his own head full of thoughts. “I’ve um got a condom” he says breaking the train of thought. Bending down into his utility belt. “Jedi standard issue” He jokes lightly and you laugh, breaking the tension. “For the space STDS and preventing children across the universe” you respond. You see his hands shaking and for the first time, you see how hungry his pupils were, despite his polite and somewhat shy demeanor. He sneaks a kiss then stands back up and rolls the condom on. The view driving him crazy. You hover your hand over his length. You can feel it throbbing as you wrap your fingers around it, unable to fit whole thing in your hand. He gives a shutter and shows the smallest fraction of a restrained buck into your hand. “Your not going to break it” he saw with a grin at your feather light touches. His hair framing his face as he looks down at you. Your mouth hangs open a little bit and you clench your thighs together, trying to get relief from the ache. You wanted to suck him off, see him moan, make him cum. You couldn’t get any words out of your mouth and he seemed to know.

Reaching down a thumb to caress your open lip. You move your face close, letting a hot breathe roll down it, giving a test lick. He grabs the bed behind him in effort to not push forward. You put your lips to the tip and suck lightly. Slowly sucking, bobbing your head like you’d seen in the videos. Reaching a hand up to where you can’t reach at the base. He lets out a groan. Hand resting on your head trying not to pull your hair. You take him deeper, aroused as the sight of his eyes shut and brow furrowed. Lips slightly parted. Your jaw begins to relax. “t-Teeth! Watch your teeth love” you open you mouth and fold your lips under your teeth, watching his shoulders drop relaxing again. You can feel the veins and ridges with you tongue, you try a few different things exploring before trying to take him even deeper. You gag hard choking. He pulls back immediately and crouches down to your level holding your shoulder. “Your okay, breathe through your nose” you nod swallowing down your spit and sniffling a bit, eyes watery. His full of concern. “Come now” he pulls you to stand, and pushes you gently to sit on the bed. Feeling bad despite it not being his fault. Kissing you gently “lay back darling” he kisses down your neck leaving bites and bruises to your breast bone. You raise you chest wanting more. He moves sucking on your breasts gently biting your nipples, indulging himself, squeezing like a cat kneading a pillow.  
Caressing the soft flesh. Your womanhood was throbbing now, needing attention. You squeeze your legs together, feeling the slick spread on your thighs, hating the sticky wetness. He moved down to your pelvis but you shut your legs together. Realizing suddenly quite how vulnerable you were. “I’d rather, try that another day...can you.. maybe use your fingers?” You ask earnestly and he stutters “ya of course” trying not to seem intimidating he sits to the side of your legs. You still feeling embarrassed at the thought of someone seeing yourself fully exposed. He traces his finger down in between your legs. Looking up for a moment to see you reaction.

You pull your legs up so they’re bent, but knees still together trying to shield your modesty. He snakes a hand under accommodating you. You can see his ears turn red and his fingers feel how wet you are, at seeing you like this, and you seeing him. If there wasn’t so much blood in his dick it would be in his cheeks. “Relax your body” he says lightly and he tests your clit. You jump, no one ever touching you there before. He applies more pressure with his calloused pads, testing the water, circling slowly while watching your face. One finger prods at your entrance while still slowly working your clit. He was usually such a smooth talker, but now he seemed so entranced and slightly timid. He curls his finger, slowly inching his finger deeper. You let a shaky “haaaa” His thumb speeding slighthy. Before you even realize it’s happening you buck harshly off the mattress with an ugly squeak of pleasure. “I..wow keep doing that” you pant out, unable to ever reach that deep with your own fingers before. Slowly using one hand to stimulate his erection, He gradually works a second long finger inside you, slowly scissoring his fingers every now and then to prepare you. He was always an attentive lover, despite not being extremely versed. It was just by his nature. He’d never taken a girls virginity before and he was going to prep you the best he could. After a few moments of this and several groans seeping though your lips he slowly pulls his fingers out. Wiping your glistening slick on the sheets. The feel of emptiness is odd. He sits infront of your knees, you part them slightly. “Are you sure you’d like to go through with this, we can always come back to this” he says eyeing your nervous face. “No I want this, just... be gentle” you say trying not to let your voice crack. “I will” he responds looking into your eyes. You allow him to part your legs so he can slide between them. He kisses you sweetly “I would never try to hurt you. Please be communicative if you do feel discomfort”

your heart is racing, hoping he’d just get it over with. You tense your body in preparation “Your knees are in my kidneys love” he chokes out smiling, in your haze you where cramping your legs shut with him in the middle. “Sorry” you smile embarrassed and let him take lead, relaxing your body the best you could. He grabs you hips and shifts a bit. One hand spreads your folds gently and the other he uses to guide the tip, first rubbing in your slick. He pushes in gently and slowly. You stare up at the ceiling “breathe” he says as you realize you were holding your breathe. He pulls back a bit pushing in again a little deeper this time, and then deeper again, you let out a whimper and grab the sheets. He stays still for a moment leaning forward to hold your hand a bit. Your nerves alone were constrincting your body. The stretch was good and felt like feeding a primal need, but your worries were getting the best of you. You nod after a few breaths and he continues studying your face, it’s easier now. He coos sweet praises as you take him. It stings but doesn’t feel like he’s breaking your pelvis or tearing you open. His patience benefiting you. The feeling is strange but not unwelcome. He pulls out a bit and pushes back in again, this time hips flush with yours. The tip of his cock taps your cervix and jump a bit. Noting this you both sit unmoving. He tells you dirty things, that are yet so poetic. A master at telling you naughty words in a voice that makes it sound so beautiful. Allowing your body to adjust to the foreign intrusion. Your cervix retracting as your arousal increases. He shifts his hips and you can feel everything. You let out a small mmmm. You rub your clit on his pelvic bone. It feels so good but still hurts a bit when you try to wiggle for more friction. “Try not to clench” he says and you clench down on him as he’s saying the words and it burns. Tears pricking at the side of your eyes. He shakes his head with a sigh kissing your neck. His cock throbbing inside you. His hands roam your body for a few moments letting the burn subside. You can’t wait any longer. “P-please Obi Wan” you whine, you realize how pitiful and desperate you sound.

When he feels your body has relaxed sufficiently, he moves ever so slowly, little by little. His body caging you with either hand placed by your head. He realizes you might feel a bit trapped and moves back down grabbing your hips instead. Guiding them to where you two meet. He rolls his hips slowly upward “is, is this ok” he asks looking up from your pussy. Mesmerized by how your body takes all of him, no longer rejecting him “You can go faster” you say with a sparkle in your eyes, eyes that squint shut soon from the pleasure after as he slowly introduced you to a quicker pace. He’s picking up speed but still holding back. You bite your cheek at the wet squelching. The creaky bed. The sound of body’s slapping, Obi Wans panting above you, alternating between watching your face and his cock stretching you open. 

The pain is but a dull ache that’s barely even noticeable. Almost entirely pleasurable as he rocks in and out of your body. Every now and the shifting squeeze your thighs of ass. His pace is moderate controlling himself, not wanting to slam into you for your first time. Feeling every detail of his length you start to whimper. “There we go” he whispers half to himself. Angling his hips to meet in the same sweet place. He takes a hand and starts playing gently with your clit. You reach up grabbing his hair and pull it with a high pitched cry of pleasure that trails off. He lets out a groan as your pussy tightens around him. Both sweating and moaning. Sinful sounds and sights and smells. You keep this up, your body getting sore and tired, nails gripping at his back as he pleasures you grunting, dragging himself in and out. You had never gotten it this good before. You start to peak, whining his name, you can’t keep this up much longer your so tired and sore. Your so close then it slowly dies away just unable to grasp your finish. A few more thursts and he cums into the condom with a groan. Subtly shaking. Staying inside you a moment breathing heavy, brushing your hair out of your face. “I can finish you off” he says pulling out slowly, going to rub your clit but you were so exhausted. The sheer nervousness alone had drained you completely.

“Please just lay with me” you pant out. He gives you a kiss then throws out the condom and pulls his underwear back on. Grabbing you a fresh pair and a large tshirt. “Let me clean you a bit” he says using a towel to wiping the little blood and natural lubricant from your body. Then throwing your clothes at you. “You’ll probably be a little sore tomorrow and it’s not uncommon to spot some blood” he says while climbing into bed with you. “You need to go pee” he says in a rather demanding way. “I’m so tired Obi” you counter and he gives you a shove with a cold foot on your back. You get up with an “EEK” “your the one who said no socks” he retorts. You hover for a second “thank you, for this. It meant a lot to me” you say open heartedly. “Next time will be more fun, I promise” he says before giving you another shove.


End file.
